Synthesis of an mRNA Fragment of Alanyl-tRNA Synthetase Gene in Escherichia coli Using the 6-Methyl-3-pyridyl Group for Protection of the Imide Functions of Uridine and Guanosine.

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Abstract
The synthesis of 5''-GpGpUpGpU-3'' is reported to demonstrate the synthesis use of the 6-methyl-3-pyridyl group for the protection of the O-4 and O-6 imide functions of uridine and guanosine, respectively. The 2''- and 5''-hydroxyl functions and the key intermediates were protected with two acid-labile groups: 3-methoxy-1,5-dicarbomethoxypentane-3-yl (MDMP) and 9-(4-octadecyloxyphenyl)xanthen-9-yl (C18Px), respectively. The internucleotide phosphotriesters were protected with 2-chlorophenyl and the 9-fluorenylmethyl group was employed for 3''-terminal phosphate protection.